Dimethylformamide dimethyl acetal → 4-[[(Dimethylamino)methylene]amino]-3-pyridinol

HRID 399384Notes

Reaction equation

HRID 399384 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>>[CH3:11][N:12]([CH:14]=[N:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8])[CH3:13]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27624194-Amino-3-hydroxypyridine

Product 1

HCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

Procedure

A solution prepared from of 4-amino-3-pyridinol (1.10 g) and 10 ml of N,N-dimethylformamide dimethyl acetal was refluxed for 30 minutes. At the end of this time, the reaction mixture was concentrated under reduced pressure and the residue was passed over a short column of florisil, eluting with 5% methanol/ethyl acetate. The eluate was concentrated and the residue and recrystallized from ethyl acetate/pentane to afford 0.91 g of analytically pure product, m.p. 121°-123°.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. concentrationAt the end of this time, the reaction mixture was concentrated under reduced pressure
  3. washeluting with 5% methanol/ethyl acetate
  4. concentrationThe eluate was concentrated
  5. customthe residue and recrystallized from ethyl acetate/pentane
  6. customto afford 0.91 g of analytically pure product, m.p. 121°-123°

Sources & evidence

ORD record
ord-c7549c50806e4d319dd776dc41296259
Source dataset
uspto-grants-1998_10
Patent number
US05821239

Reaction notes

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